Issue 14, 1999
From the journal:

Chemical Communications

Catalysis of chlorosilane on the ring-expansion of cyclic acetals bearing a carbene precursor. Lewis acid–base effect on the oxonium ylide intermediate

Takashi Mori  and  Akira Oku  

Abstract

Rhodium catalyzed (1–0.1 mol%) decomposition of 2-(3-diazo-2-oxopropyl)-2-methyldioxolane 1a or 2-(3-diazo-1-methyl-2-oxopropyl)-2-methyldioxolane 1b in the presence of a catalytic amount of TMSCl (10 mol%), yielded 4,7-dioxocane 3a (91%) or 3b (49%), whereas similar reaction in the absence of TMSCl caused 1,2-rearrangement to give bicyclobutanones 2a or 2b, respectively; Lewis acid-base catalysis by TMSCl of the ring-expansion of a bicyclooxonium ylide intermediate is revealed.

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Article information

DOI
https://doi.org/10.1039/A903928G
Article type
Paper

Chem. Commun., 1999, 1339-1340

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Catalysis of chlorosilane on the ring-expansion of cyclic acetals bearing a carbene precursor. Lewis acid–base effect on the oxonium ylide intermediate

T. Mori and A. Oku, Chem. Commun., 1999, 1339 DOI: 10.1039/A903928G

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